Diethyl azodicarboxylate → 4-isopropyl-6-[5-(phenylmethyloxycarbonyl)pentyloxy]-2-(1-phenyl-3-trifluoromethyl pyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

HRID 1289870Notes

Reaction equation

HRID 1289870 reaction equation
[CH:1]([C:4]1[C:9]2[C:10](=[O:32])[N:11]([CH2:15][O:16][C:17]3[N:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:20]=[C:19]([C:28]([F:31])([F:30])[F:29])[CH:18]=3)[S:12](=[O:14])(=[O:13])[C:8]=2[CH:7]=[C:6]([OH:33])[CH:5]=1)([CH3:3])[CH3:2].[C:34]1([CH2:40][O:41][C:42](=[O:49])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]O)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl>[CH:1]([C:4]1[C:9]2[C:10](=[O:32])[N:11]([CH2:15][O:16][C:17]3[N:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:20]=[C:19]([C:28]([F:29])([F:30])[F:31])[CH:18]=3)[S:12](=[O:14])(=[O:13])[C:8]=2[CH:7]=[C:6]([O:33][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][C:42]([O:41][CH2:40][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:49])[CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 5462977Diethyl azodicarboxylateHCID 15224618Benzyl 6-hydroxyhexanoateHCID 189225714-isopropyl-6-hydroxy-2-(1-phenyl-3-trifluoromethylpyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 676415584-isopropyl-6-[5-(phenylmethyloxycarbonyl)pentyloxy]-2-(1-phenyl-3-trifluoromethyl pyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxideYield 29.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-isopropyl-6-hydroxy-2-(1-phenyl-3-trifluoromethylpyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (6 g; 12.46 mmol), 6-hydroxyhexanoic acid phenylmethyl ester (4.2 g;14.96 mmol), DEAD (4.35 g; 24.9 mmol) and(Ph)3P (6.54 g; 24.93 mmol) in methylene chloride (100 ml) was combined with cooling in ice/water and then was stirred at room temperature overnight. The mixture was concentrated in vacuo and the residue was purified by flash chromatography (silica gel; 20-80% ethyl acetate/hexane) to afford 2.5 g (29%) of 4-isopropyl-6-[5-(phenylmethyloxycarbonyl)pentyloxy]-2-(1-phenyl-3-trifluoromethyl pyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =Ph; R2 =CF3 ; R3 =H; R4 =CH(CH3)2 ; R5 =6-O(CH2)5C(O)OCH2H) as a solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by flash chromatography (silica gel; 20-80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e06aba2b49f743ae908c4edf932c5dab
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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